(S_S,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide

Base Information

• Chemical Name: (S_S,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide
• CAS No.: 1366005-12-0
• Molecular Formula: C₁₇H₂₅NO₂S
• Molecular Weight: 307.457

Synonyms:(S_S,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide

Chemical Property of (S_S,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide

Chemical Property:

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Technology Process of (S_S,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide

There total 4 articles about (S_S,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

(1S,2S,5R)-2-isopropyl-5-methylcyclohexanesulfinamide + salicylaldehyde (90-02-8) → (SS,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide (1366005-12-0)

Guidance literature:

With toluene-4-sulfonic acid; copper(II) sulfate; In tetrahydrofuran; at 20 ℃;

DOI:10.1134/S1070428012020066

Reference yield:

(1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfenamide → (SS,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide (1366005-12-0) + (RS,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 20 ℃; for 3h; Reagent/catalyst;

DOI:10.1007/s11172-013-0343-3

Reference yield:

salicylaldehyde (90-02-8) → (SS,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide (1366005-12-0) + (RS,1S,2S,5R,E)-N-(2-hydroxybenzylidene)-2-isopropyl-5-methylcyclohexanesulfinamide

Guidance literature:

Multi-step reaction with 2 steps

1.1: ammonia; N-chloro-succinimide / tetrahydrofuran / -40 - -35 °C

1.2: 12 h

2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 3 h / 20 °C

With N-chloro-succinimide; ammonia; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform;

DOI:10.1007/s11172-013-0343-3

upstream raw materials:

salicylaldehyde

(1S,2S,5R)-(+)-neomenthyl thiol

Downstream raw materials:

(S,1S,2S,5R)-N-(2-hydroxybenzyl)-2-isopropyl-5-methylcyclohexanesulfinamide

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